


Are you free tonight?

by taebo



Category: Supernatural
Genre: Daddy!Cas, Destiel - Freeform, Fluff, M/M, Young!Dean, babysitting au
Language: English
Status: In-Progress
Published: 2015-03-01
Updated: 2016-08-25
Packaged: 2018-03-15 18:47:48
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 5,296
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3457853
Author URL: https://archiveofourown.org/users/taebo/pseuds/taebo
Summary: <blockquote class="userstuff">
              <p>Dean didn't know what he was thinking when he agreed to Sam's idea of babysitting for some extra money. Though when he got his first call from Castiel to watch his five year old daughter, he had no idea things would go as they did.</p>
            </blockquote>





	1. Chapter One: Dean

**Author's Note:**

  * For [lemonsorbae](https://archiveofourown.org/users/lemonsorbae/gifts).



> This is my first fic, so I hope its not to horrible. I'm writing this for angelwingsandthings and I hope she like them. I want to make this better as I go, so please feel free to offer any suggestions or advice!

Dean didn't know what he was thinking when he put that ad up. Babysitting? Him of all people babysitting? Eighteen with that cliché bad boy look to him. Yeah that was the sort of person you trusted to watching your little bundle of joy. Though his younger brother Sam has suggested it and well who was he to oppose extra money to his college fund? Well that was if anyone would actually call him. It had been a week or so and no one seem to even notice the ads he had put up around town. He scowled as he glanced at his phone for at least the tenth time that day alone. Maybe he should get online and see if anyone is willing to hire a soon to be high school graduate with no real college plans just yet.  
He had just started up his computer when he nearly fell out of the chair from the sudden loud buzzing from his phone. He looked over and saw it was a number he didn’t recognized. Picking up his phone he hit answer and brought it up to his ear. He honestly expected this to be some classmates or something making fun of him.

“Hello?” he questioned leaning back in his chair.

“Is this Dean Winchester? The one that put up the babysitting ads?” he was rather surprised by the deep voice that came across speaker, He could sit here and listen to it all night. The male questioning if he was still there was his cue that he had been quiet for too long.

“Oh sorry, yeah that’s me. Who is this?” It didn’t sound like any of his classmates trying to pull a prank.

“Castiel Novak. I got your number from an ad you must have put up? I was hoping you were available to babysit tonight? Mine cancelled last minute, and my other backups are unavailable. So you’re my last hope.” Castiel explained. This really surprised Dean, this man’s name sounded familiar. Thinking now, he knew his mom would be a little upset that he missed dinner, but if he did a good job perhaps Castiel would recommend him to others.

“Yeah I’m free. What’s your address? I could leave now if you needed me to.” Dean offered getting up from his chair and grabbing his leather jacket from the back of his seat.  
“Oh that would be wonderful.” Castiel gave him his address before ending the call. Slipping his phone into his pocket he made his way out of his room. Once he was downstairs he could hear his mom in the kitchen humming ‘Hey Jude’ as she made dinner. He leaned against the door frame of the kitchen and smiled as he watched her. He could never ask for a better mother, even when he came out as bisexual last year, all she asked is if he would like some pie after dinner. His father was a bit more conflicted about it but never shunned him or anything. Dean felt he was coming to terms with who Dean was.

“Hey mom. I just got a babysitting job for tonight so I won’t be home for dinner. That’s not a big problem is it?” he question, he knew she be slightly upset that it was so last minute but he doubted she stop him.

“And how long have you known about his?” Mary asked as she turn to the side some to look at him. Placing her hand on her hip.

“I just got off the phone with them. His name is Castiel Novak and he actually just lives a few streets over.” Dean explained as he started to pull his jacket on.

“Oh Mr. Novak! He’s such a sweet man, and his little girl is just adorable. Just make sure he knows it’s a school night so you can’t be there all night. I’ll keep some dinner saved in the oven for you.” She stated while turning back to the stove. Dean laughed a little under his breath and nodded, moving away from the door frame.

“Thanks mom. I’ll let you know if I’m going to be getting home late.” With that he grabbed the keys to the impala his dad had given him for his sixteenth birthday. He loved that car, it was his baby. Even more so since him and John had spent the better part of a few summers getting it back into working order. It was his Baby.

It was a short drive before he reached the address Cas had given him. It was a simple two story house that could use a little yard work honestly. Dean parked in the street and made his way up the walk way towards the stairs. He noticed this little eco-friendly car in the drive and chuckled a little. He started to get this mental image of what he thought Cas looked like, though the way his voice sounded he was having a hard time picturing him drive that car. As he made his way up the stairs to the front door he noticed a small wind chime that had little bees hanging from it next to the door. Even the welcome mat at the door had a few bees on it. Dean quirked a brow and shook his head some before ringing the door bell and waited. 

He could hear some rustling around from the other side of the door. After a minute or so the door open revealing the little girl he assumed he would be watching. Her light blonde hair was a mess of curls and her bright blue eyes held the intense curiosity as she looked him up and down.

“…. Papa! “She called moving away from the door looking towards the stairs. Dean could hear someone making their way down the stairs before he saw a pair of black slacks and black socks trying to hurry down the stairs. His heart nearly stopped when he saw the rest of the body making its way down the stairs adjusting his tie. That mess mop of short brown hair, those intense blue eyes. The small amount of scruff on his face. This was not the man Dean was expecting. He been expecting maybe someone older, possible late thirties early forties. Not someone who looked maybe in their late twenties. The little girl sort of skipped away from the door and hugged on to Castiel’s leg and smiled up at him.

“Is this my babysitter for the night papa?” she asked looking back over to Dean.

“I believe so. Dean?” Cas asked messing with his tie a bit more. Dean nodded and stepped into the house shutting the door behind him.

“You must be Castiel? And this is your daughter?” Dean question as he bent down some so he was level with the little girl. She smiled a bit of a shy smile and hugged a bit more on to Cas leg. Cas smiled down softly at her and patted her mess of curls lightly.

“This is Emma. Can you say hello?” Emma looked up to Cas and then back to Dean before slowly moving away from his leg and over to Dean. She looked him up and down, seeming to be deep in thought.

“…. Hi Dean. Do you like Tinkerbell?”

“Do I like Tinkerbell? What kind of question is that? I love Tinkerbell.” The smile Emma got spread from ear to ear and she nodded as if she approved of him. Dean looked up when he noticed Cas was closer. He had to bite his tongue some to keep from gasping some. He was smiling and just something about it took Dean’s breath away. Dean cleared his throat as he stood up slowly and moved back a bit.

“I hope you’re not planning to be out all night? I have school in the morning and my mother will be pi-… upset if I get home really late.” Dean had to catch himself since he wasn’t exactly sure how Cas felt about cursing or anything like that around his daughter. Cas just shook his head some and moved over by the door starting to pull on some dress shoes.

“No I should only be gone a few hours really. Hopefully I’ll be back before Emma’s bed time. Though if I’m not, it’s at nine. Do not let her trick you into giving her candy or any sweets. I left some money on the counter for pizza. There is a list of numbers next to the money of where you can get ahold of me if there is an emergency. Emma blah….. Blah blah blah blah… blah blah….” Dean had slowly stop listening to Cas as he went on. He just kept watching those lips, and his mind would drift a little. He only noticed Cas had moved, when he bent over and kiss Emma’s forehead. Dean’s eyes trailed down Cas’ back slowly and then he stared at that ass for some time. He had gotten a rather pleasant mental image of that in in those pants when he hear Cas say his name. Dean snapped back to reality and was faced with a rather darkly blushing Castiel. He had been caught and could feel any hope of him ever babysitting for Cas ever again withering away to nothing. Dean’s blush was matching Cas rather quickly as his eyes drifted to the floor. Neither of them noticed Emma looking between them getting a rather curious look to her bright blue eyes.

“…Well like I said there a list of numbers if you need to get ahold of me. I shouldn’t be too late.” At that Cas turned and pulled on this tan trench coat that looked like he had it for a while, which honestly the coat seem to suit him. Emma and Dean watched Cas leave from the door before she skipped off to the kitchen. Dean followed after her and looked around the kitchen some. It was simple and you could almost tell the microwave was used far more than the stove. 

“So what sort of pizza do you like Emma?” Dean asked as he picked up the money and list of numbers from the counter. Emma poked her head out from the fridge and thought a moment, before she stepped back with the gallon of milk. Struggling slightly. Dean set the money and list down and moved over taking the jug from her with a smile and moved it to the counter.

“I like pepperoni. And glasses are in that one.” She said pointing to one of the cabinets to Dean’s left. He poured her a glass of milk and handed it to her.

“Well pepperoni it is. Do you like cheese sticks?” he asked as he pulled out his phone and got the number to one of the closes pizza places that deliver. He a big yes from Emma, which made him laugh. While he ordered the pizza Emma wondered off to the living room to pick out the moves she wanted to watch, Dean picked up the list of numbers Cas had left expecting a restaurant or theater or someplace like that. Seeing how he figured Cas was going on a date. He was surprised to find it was a few number and extension to the local college. Hot and smart? Wonder if he is taking classes or teaching them… Dean question to himself as he set the list down.

It wasn’t too long after that the pizza arrived and the pair of them were on the couch slowly eating pizza while Emma was engrossed in the third Tinkerbell movie so far about pirates or something like that. Dean wasn’t really paying attention. Neither of them heard Cas come in, so when he reached between them from behind the couch and grabbed one of the bread sticks from Emma’s plate the both jumped.

“Papa!” Emma cried ecstatically putting her plate down on the coffee table as she hopped off the couch. She rounded in quickly and was hugging on to his leg at break neck speed. Dean couldn’t help but chuckle a little.

“Hello my little bumble bee. Were you good for Dean?” he asked patting her head and looking to Dean. He nodded and stood up.

“She was very well behaved.”

“Well that makes me happy to hear. Why don’t you run on upstairs and start getting ready for a bed?” Cas asked looking back to Emma. She groaned but nodded and made her way out of the living room and upstairs. Leaving Dean and Cas alone.

“Thank you for coming on such short notice Dean. I don’t know what I would have done if you had said no.” he ran a hand through that already messy hair. Dean could tell he looked tired and honestly started to wonder what it was Cas did.

“Hey it’s no problem really. Mean I wasn’t about to pass up my first babysitting job.” Dean said with a small laugh as he picked up his leather jacket he had taken off earlier.  
“So are you like some professor or something?” Dean asked as he started to pull on his jacket.

“Yes I am. I teach a course on theology, but I also do research on it. That is why I was there tonight. I had some research I needed to get a bit further on. Though I doubt you want to hear any of this. I tend to ramble and I wouldn’t want to keep you too late.” Cas reached into his pocket and pulled out his wallet before handing Dean about sixty bucks. Dean started at it and shook his head.

“No that’s too much I couldn’t take that.”

“I want you to have it Dean. I wasn’t joking when I said I didn’t know what I would have done. And while I haven’t talked to Emma about how well you did, I get the feeling you’ve earned it.” He said as he walked over to Dean and put the money in his hand. For a brief moment Cas’ fingers brushed over Dean’s wrist and a slight shiver ran up Dean’s arm.

“I umm… I… Thanks… I should go. Don’t hesitate to call me if you need a babysitter again. Emma is really a sweet girl.” He said with a smile as he slipped the money into his back pocket. Cas nodded and followed him to the door and held it open for him.

“Thank you again Dean. I will keep you in mind next time.” With that Dean left and made his way back home. He was sure his mother would be disappointed that Dean had pizza instead of her dinner, but he could figure he could eat it for lunch tomorrow.


	2. Castiel

Cas walked Dean to the door and watched him until he was in his car. After that he shut the door and yawned a little. He could hear Emma shuffling about in her room getting ready for bed and he just smiled to himself as he pulled off his trench coat. Once he had hung it up and kicked his shoes off he made his way upstairs. He paused outside the white door that was covered in various stickers of Tinkerbell and little bees, and Emma in large silver sparkly foam letters. He knocked and waited until he heard her say he could come in.

“Are you all ready for bed Emma?” he asked opening the door and stepping inside. The little girl was just climbing into bed holding a book and pulling her little light up bee into her arms. She nodded as she settled into her pillows and Tinkerbell comforter, before she held out the book.

“Will you read me a bedtime story papa?” her blue eyes wide and fully of hope. Cas couldn’t help smile. He walked over to the simple white framed twin size bed and sat on the edge of the bed.

“Of course. What did you pick out tonight?” he asked taking the book from her. Emma scooted over so Cas could sit next to her and she could cuddle up to him.

“Where the Wild Things Are of course! “ Emma said with a small giggle and settled comfortably into Cas side. He couldn’t help but shake his head as he put his arm around her and open the book. For what had to bed the eightieth time that week. He knew she wouldn’t fall asleep but it was their nightly ritual. That sat there like that until Cas finished reading and closed the book looking down at Emma. She yawned and then looked up at him.

“Again?” she asked, her eyes already pretty heavy with sleep. He shook his head and set the book on the nightstand next to her bed.

“Sorry my little bumble bee. Its bed time. Now get comfortable.” He said as he pulled away and then turned to face her bed. He waited until she was laying down and was comfortable. He tucked her in, and then pressed the little button on her bee that now rested next to her, that made it project the stars and planets on the ceiling.

“Are you tucked in all nice and tight?” he asked as he leaned in and kissed her forehead.

“Yes papa…. Can I ask you something?”

“Of course. What is is?”

“Can Dean be my new babysitter from now on? He was really fun. Meg doesn’t watch Tinkerbell with me.” She said pouting some. Cas just smiled at her and brushed some of that curly blonde hair out of her eyes.

“We will see. Dean has school like you do and I’m sure he has school activities to do. So I can’t make any promises. Goodnight sweet heart. “He said softly and he stood up and turned her lamp off next to her bed.

“Good night papa.” She yawned as she closed her eyes. With that Cas slipped out of her room and made his way across the hall to his room. He sat down on the bed and couldn’t help but sigh some. Being bent over books for hours a day was surprisingly taxing. He ran a hand through his hair before he got up again and started to undress. He was thankful that his morning class was later in the morning, so it gave him a chance to sleep in a bit. Well that was if Emma would let him. Not something he was going to really hold his breath on. Once he disposed of his cloth in the hamper, he made his way into the master bathroom that was just off his room. He stepped into the shower and relaxed once the water was suitable enough. He stood like that for a few moments, eyes closed just letting the warm water run over the back of his neck and body.

Slowly his mind started to drift to today’s events just to make sure he didn’t forget to do something important. When he got to when Dean showed up and the few moments that were spent with him before leaving, he had been slightly zoned out. He thought about those freckles and the greenest eyes he had ever seen on anyone. And when he blushed when he had caught him staring. Though it was the water starting to get cool that brought him back to reality and he shook his head. He could not be thinking about his eighteen year old babysitter he just meet tonight like that. He was trying to be a good father to Emma and becoming one of those sort of dads that hook up with the young babysitter was not him. He could think of a few of his colleges and friends that would do something like that though. He turned the water up some to get it warm once more and quickly finished up his shower.

Once he was out and dress, he laid back in his bed relaxing into the mattress. He glanced over to his phone and picked it up making sure his alarm was set before setting it back down. From there he drifted off to sleep. It had only felt like he been asleep five minutes before he felt the bed moving and felt a small body flop down on his chest. He groaned and slowly open his eyes seeing his morning sun filled room and Emma laying on his chest smiling at him.

“Good morning daddy!!” she said giggled before sitting up.

“Good morning sweet heart. Though surely you could have woken me up by not jumping on me?” he question but smiled at her. Emma pretended to think about it before she sat up and shook her head.

“Nope! That seem to be the most effective way. Uncle Jimmy down stair making breakfast.” She said before crawling off his bed and skipping off down stairs he assumed. Once she said that he could hear the sounds of cooking down stairs and could smell something he assumed to be French toast. He yawned and sat up. He had to sit there a moment and rubbed his face before he got up and made his way down to the kitchen. He looked around sleepily and then found what he was looking for. He made a bee line for the coffee pot that he could smell fresh coffee.

“Good morning brother. I take it you were up late again?” Jimmy asked looking over from the stove where, as Cas had guessed was French toast in the process of cooking. Once he had a coffee cup filled with coffee he turned and leaned against the counter squinting over the cup to his twin brother.

“Not as late as I could have been. Emma was put to bed close to her bed time once I got home.” He mumbled taking a large drink from the cup.

“Got home? I thought Meg cancelled?” Jimmy asked looking at him confused, moving some of the pieces of toast to a plate.

“She did! But daddy was able to find a new babysitter and he was really fun Uncle Jimmy! He even watched Tinkerbell with me, and not pretend to watch he actually watched.” Emma chimed in from her spot at the table eating some orange slices while she waited for French toast.

“Oh? He sounds like a keeper. What’s his name?”

“Dean Winchester. I believe his mother and brother go to the same church as us.” Cas explained. He assumed Dean was the older son to Mary Winchester who he saw whenever he actually made it to church with Emma and Jimmy. Sometimes he got a little occupied by his work.

“Really? From the way Mary talked about him I didn’t picture him the babysitter type. Do you think you’ll have him babysit again?” Jimmy question before shutting of the stove and moving over to the table with the plate of French toast and sitting down next to Emma. Cas moved away from the counter and joined them on the other side of Emma, helping not drowned her breakfast in syrup. He could see that hopeful look in her eye and the possibility of having Dean babysit again. Cas had to sigh some.

“Maybe. He still in High School so I can’t call on him like I can Meg or You.” He explained glancing to Jimmy, “So if he is free then I don’t see why he can’t watch Emma.”

“Yay! I can’t wait until you have to work again daddy!” Emma cheered before taking a large syrup covered bite of toast. Cas just smiled and shook his head.

“Thank you for that bumble bee. Nice to know you have much more fun with you babysitters then me.” He said with a small laugh. Jimmy was just smiling over his breakfast. This was their normal routine. Jimmy would come over in the morning when Cas had class and home school Emma and watch her until classes were over. Then Cas would come home and be with her the rest of the night unless he needed to do more research or had some project for his studies.

“I only have a few classes today so I should be home early. Did you have plans for this evening or would you like to stick around and help me get some head way on planning Emma’s birthday party. It’s starting to get close.” Cas question. Jimmy thought about it a moment before he nodded.

“Yes I can stick around for a while. Do you have an idea what sort of party you would like Emma?” Jimmy asked looking over and the now syrup covered little girl.

“Ummm…. I was thinking Tinkerbell… But I’m not sure. Do you have any fun ideas?” Jimmy and Cas shook their heads and thought a bit.

“Perhaps you and I can come up with some ideas later on. Brainstorm?” Jimmy offered and Emma nodded quickly.

“We could make a list of the… ummm…. What’s that called? Where you figure out the good and bad of an idea?” Emma sat there confused now. She had that sort of look like she knew what it was but she just could think of it.

“A list of pros and cons. And that sounds like a good idea. You two can do that and when I get home we can go over it. Though daddy has to go get ready for the day. I can see you’re going to need a bath here soon.” He couldn’t help but smile at the mess his little girl was and he leaned over and kissed her forehead. He gathered up his half eaten breakfast and cleaned it up some before going off and getting ready for the day. It was shortly after that he was out the door and off to class.


	3. Dean

When Dean woke the next morning he had to lay in bed a few moments and work out that he had been dreaming. That he was not in the back of Baby with Mr. Novak with some very steamy windows. A soft groan escaped him as he rolled over to his side and grabbed his phone. It was 6 am, he could try to go back to sleep for an hour but he doubted he could after that. He laid back once more and stared up at the ceiling. He couldn’t be thinking about Cas like that, for all he knew he would never see him again, sure as hell never get him in the back of the impala. Also there was no way Cas was the type of guy that would be into him or sleep with the baby sitter. After a few more moment Dean dragged himself from his bed and grabbed some cloths, before head off to the bathroom for a shower.

A half an hour later he was making his way downstairs to the smell of cinnamon rolls. As he stepped into the kitchen he took a deep breath and smiled at his mother.

“Good morning mom. Breakfast smell amazing.” He said as he moved to the fridge and pulled out some orange juice.

“Good morning. You’re up rather early. Normally I have to have Sam roll you out of bed.” Mary remarked as she looked to Dean a little surprised.

“Yeah, I had an odd dream last night and just couldn’t get back to sleep after I woke up.” He explained while he grabbed the carton and moved to the counter and grabbed a glass from the cupboard.

“I see. I could have been something you ate before bed or something. Be a dear and hand me some apples please.” Mary requested as she finished slicing some bananas about putting them into a bowl next to her. A quick glace revealed there were other fruits in it for a fruit salad. Dean nodded and set the glass he held down and grabbed a couple apples from the bowl next to him and handed them to her. Though once he took the apples he swiped a strawberry slice from the bowl and quickly popped it in his mouth.

“Hey now. You can wait until breakfast young man. Get your juice and make sure your father and brother are getting up. “She scolded with a smile. Dean just laughed a little and nodded going back to his orange juice. Once his glass was filled and juice was away he headed back upstairs with it going to Sam’s room first and knocking.

“Yo Sammie time to get up. Breakfast is almost ready!” he called through the door. There a muffled response from the other side to which he assumed was Sam saying he was up. After that he went to head to their parents room, but he was only a few steps from Sam’s door when John exited his room. He look to Dean and seemed a little surprised to see Dean up and dressed.

“Morning son. Up early I see.” He said closing the door behind him.

“Yeah, though I should get an early start today.” Dean joked and glanced back as Sam left his room now. John just nodded and walked past, patting Dean’s shoulder before going downstairs. Sam just looked over to Dean and yawned a little.

“Do I smell cinnamon rolls?” he asked glancing to the stairs.

“Yep, there fruit salad too. So you know the best of both worlds.” Dean teased his health conscious brother. 

“That sound so good this morning.” Was the only response Dean got as Sam followed after their father. Shaking his head he felt his phone go off and pulled it out of his pocket looking at the text he just received.

‘Yo I got to cancel study group tonight. Got a date tonight unless you’d be up for a threesome? ;) –Benny’

Dean rolled his eyes now and quickly sent a reply.

‘Keep dreaming Ben. I love ya like a brother and that’s all the love you’ll get from me. ‘

‘Aw buzz kill. But we’ll get together next week before that big history test. –Benny’

‘Sounds good. I got to eat breakfast. See ya at school’

‘See ya man, and keep that threesome in mind lol -Benny’

Shaking his head he put his phone back in his pocket and headed down for breakfast.

____________________________

The day been rather uneventful normal Friday for Dean and he just leaning against the impala while he waited for Sam to get out of his debate group his phone rang. Pulling it out he saw Castiel was calling him. Needless to say he was rather surprised to be receiving a call already. Though could also be that he was calling to tell Dean he never have him babysit again because he done something horribly wrong that Emma had told him about.

“Hello?” he answered unsure now.

“Dean? Its Castiel. I was wondering if you were free again tonight?” his voice was hushed for some reason.

“Uh yea. What time would you like me to come over?”

“When the soonest you could be here? My brother and I are hoping to get to the store and get some birthday gifts for Emma.”

“Well my brother in his debate group for another ten or so minutes, so maybe half an hour to forty five minutes?” he offered glancing to the main door of the school. Though he was very relieved he was calling for a babysitter again. Maybe he wasn’t so bad at this.

“Wonderful. I’ll see you as soon as you can get here. Thank you so much Dean.”

“No problem what so ever Mr. Novak. See you soon.” With that Dean hung up and called him mom letting her know he was going to drop Sam off at home and head off to babysit again.

**Notes for the Chapter:**

> I'm so sorry this took soooooo long to put up. Life got a little crazy and I had a horrible bout of writers block. I hope you all enjoy this chapter and hoping to get more regular with my posting. Feel free to leave your thoughts of this chapter and suggestion in the comments! <3


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